


Begin Again

by Oceansoul



Series: Wildest Dreams [2]
Category: Supernatural
Genre: Alternate Universe - BDSM, Alternate Universe- No Supernatural, BDSM, Dean Has Issues, Dom/sub, Kneeling, M/M, Porn With Plot, Porn with Feelings, Semi Public Sex, Sex Club, Submission, brief mentions of past abuse, handjob, sex dungeon
Language: English
Status: Completed
Published: 2017-06-11
Updated: 2017-06-11
Packaged: 2018-11-12 20:48:42
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,271
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11169810
Author URL: https://archiveofourown.org/users/Oceansoul/pseuds/Oceansoul
Summary: Part 2 of my Wildest Dreams Series.Dean meets Cain again in the Dungeon, Cain is testing Dean as a sub."You´re eager, I like that. You just need to learn to be patient." the fingers pumped slowly in and out of his opened mouth. "It´s simple. You don´t have to think about anything when you´re with me. Just listen to me, do what I ask."





	Begin Again

He stood in the middle of the room, back straight, hands behind his back. eyes fixed on the floor. Perfect posture, at least that's what he hoped. Little did he know about Cain, his probably new master, and the expectations he had of Dean. The only thing he knew was that this was a test to see if he and Cain were compatible, if they worked out and felt comfortable with each other. 

When he had arrived at the dungeon on Thursday night, Cain had already waited in the front room, sitting in a corner on one of the black leather sofas instead of at the bar. He had told Dean about his plan for the night, testing their compatibility with easy commands and a few little tasks. They hadn't talked much, Cain had promised him to take it easy this time, that he had nothing in mind that would require further details about their likings. They would talk about their kinks and fetishes later that night, when they had decided if they wanted to meet again. Then they would set boundaries and pick out safe words (Dean had insisted on using the color code for today) But right now, the only thing Dean had to do was being obedient and showing Cain how good he could be. 

Dean felt the gazes of the other men in the room on him, a pair sitting on the chair in the same position Dean and Cain had been the last time. Another guy was strapped to the St. Andrew 's cross, a buzzing vibrator in his ass and a tight cock ring tightly bound around the base of his shaft, preventing him from coming before his Dom would be back from the bar and decided that his Subs punishment was over. Dean ignored all of them as best as he could, concentrating on keeping his position and waiting for his Master-to-be. 

He flinched when a broad hand touched the small of his back, looking up before recognising Cain and looking down again, hoping that his flinching wouldn't cause a first punishment. He had been so deep in his thoughts, missing the steps that had neared from behind. He regained position, waiting for a command. 

Cain was circling him, clearly eying his posture. He was dressed in another suit, this time a navy blue one with a white shirt and matching tie, shoulder length hair neatly groomed. He was a very handsome man, making it hard for Dean to keep his gaze down. Cain came to a halt behind Dean, pushing his legs farther apart with his foot, making it easy for Cain to reach his most intimate parts if he wanted to. The hand was back on the small of his back, he didn't flinched this time. Cains other hand wrapped around his torso and pressed against chest, right over his heart, Cain would definitely feel the fast beating of it. Dean's back straightened even more with the press of the hands. They moved up to his neck, cradling his skull from behind and arranging it to Cain's liking. 

"I want you to keep your head up, not ducked to your chest. Just keep your eyes down." Cains low voice filled Dean's ears. "I want you submissive but I want to see your face as well. And keep your back straighter." 

Dean swallowed, he thought that his previous posture was perfect but Cain only needed a few seconds to correct him. Dean already felt like he messed up. 

The hands that still cradled his head wandered down his arms, stroking them down and up again, resting on his biceps. "Your arms are perfect. Hands to elbows, just right for when you're not bound." At least one thing he did right. "Dean, you're doing great. This night is for us to accommodate. I'm not scolding you." Cain seemed to have sensed Dean's disappointment on his own mistakes. It wasn't a question so he didn't answered and just waited for Cain's next move. 

"Kneel." Dean dropped instantly onto his knees without breaking position in another way, back still straight and hands clasping his elbows. He felt Cains fingers brush over his shoulders, making him shudder slightly. "Relax." Dean sunk down onto his heels, knees parted, hands on his thighs, palms down. Cain circled him again, coming to a halt in front of Dean. His knees were pushed farther apart, cool leather of expensive looking shoes a stark contrast against his heated skin. His scrotum and half hard cock hang freely between his spread legs, then the shoe was pressing up against his genitals, heaving his junk and letting it rest against the smooth material. A hand was coming up, brushing through his hair and massaging his scalp. He relaxed further into the touch, breathing slowly, calming down.   
The fingers moved away from his hair, over his cheek to his lips, caressing them with light touches of soft fingertips before pressing against them. Dean obediently opened his mouth, letting the digits in, welcoming them with a flick of his tongue but keeping still when this movement earned him a tighter press of the shoe clad foot against his genitals. "You have a very talented mouth, you already proved that last time." Yeah right, it was simply a test of his obedience. He didn´t have permission to suck on the fingers in his mouth, he should know better. He would fuck this up before it even started. The fingers brushed against his, now unmoving, tongue while the thumb of the same hand stroked his cheek. "You´re eager, I like that. You just need to learn to be patient." the fingers pumped slowly in and out of his opened mouth. "It´s simple. You don´t have to think about anything when you´re with me. Just listen to me, do what I ask." 

The shoe dissapeared from in between his legs, letting his balls drop. "You won´t have to worry about a thing when you´re with me." The fingers left his mouth, Cain not touching him anymore and even though it was only their first real night, he craved for more, starved of the tender touch of a Dom. "Can you do this?" Cain crouched down, looking Dean straight in the face. He kept his eyes down, being good. "Can you give everything you are to me? Can you trust me?" Trust, the basis of each and every relationship maybe even more important in a Dom/Sub arrangement. "Can I?" he couldn´t stop himself from asking, it was a question he had asked himself since he agreed to meet again with a stranger. He had trusted his last Master and damn, he still had nightmares from the time his trust was betrayed. Could he trust another man? Could he let go and submit? He wanted to but could he? 

His last Master, this cruel bastard, would have already slapped him for talking back and so Dean flinched hard as Cain raised a hand. But instead of a blow to his cheek, the hand only cupped the side of his neck, strong and grounding but, oh so gentle. He looked at the older man with wide eyes, emerald green meeting icy blue. A similar shade of blue like the eyes that haunted him at night but far from being the same, those eyes in which he looked right now where filled with strength and warmth, dominance and affection, instead of the cold look of pure madness. "You can. If we´re to continue this, I promise I´ll give you pleasure through order and pain but never more pain than you can bear. And I can assure you that I have experience, I know what my Subs need. I just need to be sure that you´re willing to try it." He wanted to try it yes, but could he? Could he forget about what happened and give himself to a man he barely knew? How would he ever know if he says ´no´ right now? 

"Yes, master. I wanna try it. With you. But there are things..." a finger laid upon his lips stopped him from saying more. "I told you at the start of this scene that we would set our rules later and that I wouldn't do anything that would require to talk about limits. Take this as a first exercise in trust." Dean nodded slightly, even though he felt nervous now. Maybe it was reckless to agree to this, especially with what had happened to him but he had missed being on his knees. Simply watching others during their scenes had never been fullfilling, just an outsider, a watcher. But he craved to please, a character trait only a few people could understand, one he had always kept hidden, only able to live it out in the dark of the dungeon. “Colour” asked Cain and green was Dean's answer.

Cain stood up again and strode to the armchair which was now free, Dean hadn't noticed when the couple had left. The guy on the cross was still there, sobbing and pleading. Dean followed Cain with his eyes, taking in the perfect form of the older man, the elegant way his body moved, the perfectly fitting suit (a suit in a sex club - nothing you see every day). Cain sat down and signaled Dean with two fingers to come over. He wasn't told to walk so he stayed on all fours and crawled over to Cain, trying to keep his movements smooth and graceful. He came to a halt right in front of the chair and sat up again, kneeling, knees parted wide, hands on his thighs, eyes cast downwards but head held high.

"I want you to touch yourself." Cain didn't want to waste anymore time and teasing wasn't on the plan tonight so he got to the exciting point right away. Dean´s right hand moved to his half hard cock as if it had his own will, he felt himself dive further into the feeling of submission, it was so easy being on his knees and doing what he was told. In this moment, he realized why he could do it with Cain but not with any of the other guys he had tried after his last master: they had been dominant, had given orders but they broke in when they realized he had problems or, when they haven´t noticed it, they had been too demanding, Dean had always felt as if there was no choice, as if their orders were infinite and he had felt as if he was crushed, his lungs had not allowed anymore oxygen in and the memories of the darkest hours of his life threatened to overcome his mind. 

But right now, he was still wary of his surrounding and of every twitch of Cain´s body but the guy was like a buoy in the stormy sea of his mind. It wasn't because he was attracted to him (well, of course he was but that wasn't the point). It was the fact that he was different. Different in every and any way Dean could think of. He seemed to have a lot of experience, he didn´t backed off even though he must had noticed Dean´s flinching, he hadn´t punished or scolded him for his faulty posture. He had given him praise for the things he did good instead of pointing out his flaws. His touches had been grounding and tender, but the most important thing was, that he hadn't given Dean a single order without a way to end it. Dean had had always the feeling that he could say no and that it would be accepted, that he wouldn't be pushed or even forced to do anything he wouldn't want to do.

And so, his fist closed around his shaft without any hesitation, his mind calm and unafraid, somehow knowing that this man was no threat, that he could stop anytime he wanted to, not bound or chained in anyway. "Spit on your hand to make it more pleasant. I don't want you to rub yourself raw." Dean did as he was told, spitting into his hand and closing it around his hardening length again. He did a few quick strokes up and down before he was stopped again. "Slower. I want you to draw it out, enjoy it, feel it." ´I want you´ instead of ´you have to´ or ´you must´, another sign that this could work, that he and his feelings would matter in this d/s relationship. 

He slowed down, letting his hand wander up his shaft, rubbing his cockhead and sliding down again all the way to the base, up again, his thumb pressing against his slit. "Just like that. You're allowed to make as much noise as you want and to move, just make sure that i have a good view." Dean had never been very vocal during sex but he let out a few low gasps as his cock finally swelled to full hardness. He spit onto his hand again, spread the lube replacement over his flesh. "Use your other hand too, cup your balls, roll and squeeze them in your palm." 

Direct instructions but not forced on him, they were more like presented as options in a calm and warm voice, not shouted or growled. He did as he was told, rolling his balls in his left hand while the other continued to work his shaft. He didn't even noticed how he was leaning back a little, legs spreading more, giving Cain a perfect view of what was happening. He had closed his eyes, missing the slight smile that had spread on Cain´s lips, completely focusing on the sensations in the lower half of his body, waiting for more instructions. "That's it, you're doing great." Dean couldn't help the moan that escaped his mouth, giving away how much he liked praise. He already was embarrassingly close, tension building up the whole week before this meeting, months that felt like ages without any sexual encounter that included something (or rather someone) else than his own body and some toys. 

His hand moved on it's own, up and down, gripping tight at the base when he felt the edge nearing, he hadn't had the permission to come yet so he held on. "Open your eyes. Look at me." His gaze met Cain´s eyes, movements stopping for a second or two, the man seemed unperturbed by the whole scene if it wasn't for the hungry look in his aquamarine blue eyes and the prominent bulge in his suit pants Dean detected when his gaze dropped for a second. He continued to stroke his flesh, more leisurely this time as if the world had slowed down when their eyes had met.

"You're allowed to come anytime you wish." A low groan formed in Dean's throat and broke free through his lips, he didn't want it to be over but it felt so good. Not just the hand on his cock, the whole scenario was excellent. Cain´s soothing voice, the way he corrected Dean, gave him orders to follow but leaving enough freedom for Dean so he didn´t felt caged for a second. He kept his eyes fixed on Cain's, his orgasm crashed over him, come spurting out of his cock, landing on the floor between his legs and - to his horror - a few drips smudged the shiny leather of Cain's expensive looking leather shoes. Not that he had any knowledge of clothing that cost more than a few bucks, but he knew very well how cheap looks and Cain's clothing looked quite the contrary. 

He looked up again and was surprised to find a slight smile decorating the other man's handsome face. With his last master, a punishment would have followed for staining him. "Very good Dean. We will work on keeping you longer on edge but for tonight, this was excellent. Come here." Dean shuffled closer, his cock slowly losing it’s hardness. Cain leaned forward, one hand cradling Dean's neck, thumb stroking over a stubble free jaw. Dean allowed himself to lean into the touch, closing his eyes and soaking up the affection and tenderness like a sponge the water. "You did good. But you made a mistake by soiling my shoe." Dean's eyes snapped open, of course a punishment would follow, maybe Cain wasn't as different from his last master than he thought? Maybe - "Clean it up." Before he could stop himself, an unbelieving "What?" came from his lips. He had thought of a beating or something else, something that would hurt. And it slightly hurt as Cain's hand tightened in his hair, but not as much as he was used too. It was a mere reminder, on who was in charge. 

“I don't like to repeat myself but I'll go easy on you for tonight's the first time you're taking orders from me. Now, clean it up or give me the color red." After a moment, giving Dean the chance to call red, the hand loosened it's grip and instead pressed Dean's head down, clearly signaling Dean how exactly Cain wanted him to clean his shoe. He let himself be pushed down until his nose hit the smooth leather. His ass was raised high, presenting invitingly to whomever might want to watch. He didn't know if anyone else was in the room, the whole time all his senses where fixed completely on Cain. Tentatively, he licked once, a strange mixing of flavours assaulting his tongue. The salty taste of his own cum, bitterness from the leather. It wasn't a pleasant taste and he should be embarrassed by the humiliating action but as he licked everything off, he wasn't ashamed. In a strange way, it felt good to be at Cain's feet, giving himself to the other man completely. He hoped that his mistakes wouldn't shoo away Cain, he would really want to meet him again.

When he was finished, he straightened up again, but clasping his hands behind his back once more, head held high but eyes cast downwards like he had learned tonight, waiting. From the corner of his eye, he could see how hard Cain was beneath his suit pants. He desperately wanted to reach out, touch, lick, anything. But he hadn't permission so he stayed still. "You're following orders very well." The older man scooted forward on the armchair, opening his pants and pulling out his hard cock. Dean couldn't help but stare at it, he always had a thing for long, thick and circumcised. They were so close now, Dean kneeling between Cain's slightly spread legs, that the blond could easily lean forward and lick at the tip but no, he had to be good, had to show what a great sub he was. "Open your mouth." Dean happily obliged, this was something he was good in, he could suck cock. But instead of pushing in and fucking his mouth, Cain held his cock inches away from Dean and began to move his hand, jerking off rough and fast. He didn't last long, already riled up by Dean's previous show. Aiming into Dean's mouth who groaned as the cum landed on his tongue and a few drips on his chin. He kept his mouth open, fighting the urge to swallow. "So good for me." Cain stroked himself lazily through his post orgasmic bliss, scooping up the cum that had landed on Dean's jaw with his forefinger, smearing it on the younger man's plush lips. He then pressed Dean's mouth shut and moved forward to press a kiss on those perfect lips. 

Their first kiss was messy, Cain demanding entrance to Dean's cum filled mouth, tasting himself and the sweetness of Dean. When he broke the kiss, he had to held Dean's head in place, stopping him from moving forward, wanting another kiss. "Clean yourself up in the restrooms, then meet me at the bar." He waited for Dean to get to his feet, steadying him when he slightly stumbled, knees aching from the long kneeling. "Thank you. Should I get dressed too Sir?" Dean asked softly, getting only a nod as response. He had to walk through half of the dungeon to get to the restrooms, real ones, aside from the bar the only place where nobody got fucked. His mind was still spinning, trying to comprehend what has happened the past hours. He took a fast shower, washing off the sweat and cum from his body. He was alone in the room which was good, he needed this time for himself. He dressed in his clothes which he had placed in one of the lockers, secured with a combination lock, and smoothed the fabric over his overly sensitive skin. Pacing through the long corridors, passing dozens of rooms each with different settings and equipment, filled with dozens of men in different stages of arousal, he finally entered the front room and found Cain sitting on the same sofa as at the beginning of the evening. 

He sat down on the other side of the table, a glass of water already waiting for him. He gulped down half of it in one sip and looked anxiously to Cain. Had it been good for him too? Dean liked it, but did Cain too? Had he been good enough to be Cain's sub? What if he had messed up? What- “Dean. Look at me.” Dean had worked himself so deep into his nervous thoughts, not realizing that Cain had already tried to gain his attention twice. “Sorry, I’m sorry Sir.” God, if he hadn't messed it up before he will now. “Drink.” An easy command, he could do this. His hand shook a bit as he brought the glass to his lips again, drinking the water slower this time. “Now breathe.” another order after he had put down the now empty glass. “You’re with me Dean?” Cain looked worried, probably considering how he could dump him the easiest way. Who would want a sub like him, who gets nervous the second he has time to think?

“You were good, really good Dean.” He had wanted to be good but he messed up he- “What?” he blurted out. “I wasn't- do you really think that?” That must be a joke, false posture, flinching, talking back, everything added up means he wasn't good at all. Cain's eyes were fixed on him, nodding. “I'm always honest Dean. I don't like being lied to so I don't do it either. I liked this evening. You already have a profound knowledge of BDSM etiquette and know at least the basic positions and commands. You respond so good to corrections and you follow orders quickly. I didn't expect you to know everything from the start. I think we could be a match Dean. I think I can give you what you need as long as you're willing to let me.” Dean looked at him with wide eyes, was that really true? Cain looked as if he was honest but could it really be that this man, this master would want him? “I...I liked it too but I...did so much wrong. Do you really want to bother with me? I'm sure you could find better subs-” he stopped when Cain's face hardened, looking displeased. Dean was amazed how much this handsome face gave away with only slight changes in the gaze.

“Dean.” he liked to hear his name spoken in that deep gravelly voice. “I asked you if you want this to continue not what you think what you did wrong. Don't assume what I think or want. Just give me an answer, honest and simple: do you want me as your dom? Yes or no.” he don't wanted to be betrayed and hurt again, he wanted to be good, to let go. He wanted to trust but could he? Maybe he could try, Cain would probably dump him after a few scene anyways, he could enjoy the little he could get, he just had to make sure to not get too attached and emotionally involved. “Yes.” 

“That's good Dean, you're good. There are a few thing we have to discuss. Are you ready for that? I need you completely with me for that, you have to know exactly what you're agreeing to.” he waited for Dean's nod before continuing.  
“Whenever we're here, you belong to me. I give you pleasure, I punish you when you're making mistakes, I dominate you. I can guarantee you, you will be satisfied. You're not my fuck toy but I decide how and when you find pleasure here. I bring you to the edge but I have no intention to ever push you over it. Even though I’ll be in charge, I only have so much power as you're willing to grant me. I expect you to obey me, I expect you to trust me to know what you need even though it may be different to what you're thinking you want. But I'm dependent on you and your honesty and your consent. You have to tell me instantly if I'm ever doing something you definitely don't want to do or can't do. I don't know you yet, we have to compare our likings and limits. This should have benefits for both of us, you're not a toy Dean. I don't see you as a spineless doll and I don't want you to see yourself as helpless. You may be submissive but you will never be helpless. There is a reason why there are safe words, I never want you to be afraid to use yours. You obey me but only to the point to where you want to. There is a difference between partially submission and complete surrender. You understand that? ” 

Dean nodded, a bit unsure at first. What he had just heard was the complete opposite of everything his last master had ever said. When he had entered the BDSM scene, he had thought for a long time that the way his first master had treated him was a standard. It took him a while to figure out that he and his friends were just cruel bastards and that there were different d/s relationships. But he had never hoped to find something like this, someone who would wait for his consent before continuing with a scene. Maybe the man in front of him would be what he had dreamt of? Or maybe he would add to his nightmares?

“You’re not quite believing what I say, do you?” Dean realised he had zoned out again, not giving an answer for several minutes. He had to shake his head, no, he wasn't - couldn't - believe anything of this. “My last master was...he didn't liked me to say no.” His mouth felt dry, he wished for a new glass of water. “Why are you here Dean? Why have you agreed to meet me again?” That was an unexpected question, one he wasn´t prepared for. He had expected questions about his past experiences, about his flinching but not this.The younger man evaluated his chances to lie but ultimately decided to be honest, just like Cain had wished. “I like the concept of letting go, you know? Giving control over to someone else, not making decisions or being responsible. And yeah,” he shrugged with a slight smirk “I like the sex. Bondage and everything, I would like to try a lot of things but...you know…my last master, he was my first and only too, did a lot of things with me, to me. For way too long I thought this was what I deserve, that this was reality and everything I heard or read about the scene was just lies and fables. So, a long time after I was free of him and finally understood that there was more to this scene than...than people like him, I visited a few clubs again, this one was my favourite, everyone was nice to me and respected instantly when I declined an offer. I was just here to look but I never engaged in any action. Well, until I saw you.” He looked down at the table, studying the wood instead of meeting Cain's gaze. 

“I can take control if you let me. I can show you how good it can be. I just have to be sure that you really want this and that you know how to say stop if you need to.” This sounded so good to Dean, too good to be true. Maybe he finally got what he wished for or maybe these blue eyes would fill with madness like he had seen before on another man. “I want it but...only here at the dungeon.” he knew most of the people here, not by name but he had witnessed once when they were helping a sub whose dom hadn't stopped after the sub had nearly shouted his safeword. He guessed, he would feel the safest here. And he had never been shy, seeing other and being seen had never been a problem...as long as he could see. “That's alright with me. We have a lot of possibilities here to try things out. But I need your telephone number or at least your email address to contact you.” Cain pulled out his phone, unlocked it and passed it to Dean for him to put in his contact details. A state of the art phone, Dean noticed. Nothing to compare to his old phone which isn't even a smartphone. He typed in his email address and phone number and gave the phone back to Cain, avoiding any touch of their fingers, unsure if Cain would want to have body contact outside of a scene. “I’ll mail you a list of things I expect of you and a checklist where you can check off your limits. I want you to take your time and be honest. You can talk to me about everything, if there are any questions or things you need from me, just text or call me. And you can always decline something, remember that” Dean wondered what Cain would expect of him. “Will I get to know your limits too?” he asked. 

“No permanent damage and nothing against the law.” Well, that was short. “Remember what I said? I'll decide what we do based on your limits. You can always ask for things you want to do but it is my choice if or when we do them.” Dean nodded, suddenly feeling exhausted. He hadn't slept the last night, to nervous of the meeting with Cain and the last hours were a rollercoaster for his feelings. “Are there any other questions right now?” Dean shook his head, he had a lot of questions of course but didn't dare to ask one. Maybe writing an email would be easier. “Good, then next week, same time?” Cain waited for another nod from the younger man before standing up and putting on his jacket. “You were good Dean, I'm very pleased with you. Do you need a ride home?” - “No I'm fine, thank you.” Before leaving, Cain smiled at Dean and nodded his goodbye. Dean sat there for a few minutes before he could clear his mind enough to leave the dungeon and walk back home. He really needed to get some sleep and maybe, just maybe, this time he would dream of warm blue eyes instead of cold ones.

**Author's Note:**

> Second Part of the Wildest Dreams series. I have more in mind (more scenes, explaining what happened between Dean and his Master, maybe a fic from Cain´s POV) but time is limited so it may take some time for another part to be uploaded. 
> 
> Also, English isn´t my mother tongue so please feel free to report any mistakes to me :) 
> 
> Prompts are welcome. As always, I´m not 100% satisfied with the story so let me know what you think of the fic.
> 
> ps: the titles of the series and it´s fics are all Taylor Swift songs...why? Because I think it´s funny to use the names of songs about innocent teenage love for gay sex stories :D
> 
> pps: Any similarities to other stories are unwanted and I don´t own the characters and I don´t earn money with this.


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